lansoprazole sulfide
lansoprasole
Conditions | Yield |
---|---|
With 2C5H8N2*VO2F; dihydrogen peroxide In ethanol at 10 - 15℃; for 2h; Temperature; Industrial scale; | 100% |
With dihydrogen peroxide; methyltrioxorhenium(VII) In 2,2,2-trifluoroethanol; water at 0℃; for 1h; Product distribution / selectivity; | 98% |
With magnesium monoperoxyphthalate hexahydrate In ethanol; water at -20 - -10℃; for 4h; | 95% |
Benzimidazol-2-thiol
lansoprasole
Conditions | Yield |
---|---|
Stage #1: 3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride; Benzimidazol-2-thiol With carboxy chlorine; sodium carbonate In methanol at 64℃; for 3h; Stage #2: With titanium(IV) isopropylate In water; toluene at 28 - 55℃; for 1.83333h; Temperature; Solvent; Reagent/catalyst; Further stages; | 98% |
lansoprasole
Conditions | Yield |
---|---|
With ammonia In water; acetonitrile at 0 - 40℃; for 3.5h; Product distribution / selectivity; | 95.2% |
With ammonia In water; acetone at 30 - 35℃; Product distribution / selectivity; | 79% |
In water at 15 - 30℃; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium thiosulfate In vanadium(V) oxide; dichloromethane; tert-butyl alcohol | 93.2% |
With dihydrogen peroxide; sodium thiosulfate In vanadium(V) oxide; dichloromethane; tert-butyl alcohol | 93.2% |
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In ethanol; chloroform |
iansoprazole ethanol hydrate
lansoprasole
Conditions | Yield |
---|---|
In water at 40℃; Product distribution / selectivity; | 93% |
With triethylamine In water; acetonitrile at 35℃; Product distribution / selectivity; | 92% |
In water; acetonitrile at 35℃; Product distribution / selectivity; | 92% |
lansoprasole
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In toluene at 0 - 10℃; for 9h; Solvent; Reagent/catalyst; Temperature; | 93% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 90 - 100℃; Solvent; Large scale; | 92.1% |
water ethanol
lansoprasole
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium thiosulfate In ethanol | 91% |
With dihydrogen peroxide; sodium thiosulfate In ethanol | 91% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 90 - 100℃; Solvent; Large scale; | 90.8% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium thiosulfate In ethanol | 90.5% |
With dihydrogen peroxide; sodium thiosulfate In ethanol | 90.5% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium thiosulfate In ethanol | 89.5% |
With dihydrogen peroxide; sodium thiosulfate In ethanol | 89.5% |
2-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]thio]-1H-benzimidazole
lansoprasole
Conditions | Yield |
---|---|
Stage #1: 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]thio]-1H-benzimidazole With tert.-butylhydroperoxide; vanadium(III) 2,4-pentanedionate In ethanol at 5℃; for 6h; Stage #2: With ammonia; sodium sulfite In ethanol; water at 25℃; for 17h; pH=8 - 8.5; | 85% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; vanadium acetyl acetonate In ethanol at 5℃; for 4h; Purification / work up; | A 79% B 0.3% |
Stage #1: lansoprazole sulfide With tert.-butylhydroperoxide; vanadium acetyl acetonate In ethanol at 5℃; for 6h; Stage #2: With ammonium hydroxide In water at 25℃; for 17h; pH=8 - 8.5; Purification / work up; Alkaline aqueous solution; | A n/a B 0.15% |
lansoprazole sulfide
lansoprasole
Conditions | Yield |
---|---|
In ethanol | 79% |
2-[[(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzoimidazole
lansoprasole
Conditions | Yield |
---|---|
sodium(hydrogen ethylenediaminetetraacetato)ruthenium(III)Cl} In ethanol; water at 50℃; for 1h; | 50% |
{Ru[(EDTA)H]Cl}Na In ethanol; water at 50℃; for 1h; | 50% |
2,3-dimethyl-4-nitropyridine N-oxide
lansoprasole
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 94 percent / tert-BuOK / 42 h / 50 - 60 °C 2: 1) Ac2O, conc. H2SO4, 2) aq. NaOH / 1) 100-120 deg C, 5 h, 2) MeOH, rt, 3 h 3: 1) SOCl2, 2) MeONa / 1) CHCl3, reflux, 20 min, 2) MeOH, reflux, 1 h 4: 45 percent / m-chloroperbenzoic acid / CHCl3 / ice-cooling View Scheme |
2-Hydroxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine
lansoprasole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) SOCl2, 2) MeONa / 1) CHCl3, reflux, 20 min, 2) MeOH, reflux, 1 h 2: 45 percent / m-chloroperbenzoic acid / CHCl3 / ice-cooling View Scheme | |
Multi-step reaction with 3 steps 1: Triphenylphosphine oxide; bis(trichloromethyl) carbonate / toluene / 6 h / 20 - 60 °C 2: sodium hydroxide / ethanol / 2 h / Reflux 3: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 0.5 h / -5 - 20 °C View Scheme |
2,3-dimethyl-4-(2,2,2-trifluoroethoxy)-pyridine N-oxide
lansoprasole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1) Ac2O, conc. H2SO4, 2) aq. NaOH / 1) 100-120 deg C, 5 h, 2) MeOH, rt, 3 h 2: 1) SOCl2, 2) MeONa / 1) CHCl3, reflux, 20 min, 2) MeOH, reflux, 1 h 3: 45 percent / m-chloroperbenzoic acid / CHCl3 / ice-cooling View Scheme |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene | |
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; ethyl acetate | |
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene |
lansoprasole
Conditions | Yield |
---|---|
With urea hydrogen peroxide adduct; vanadium(V) oxytrifluoride In 1-methyl-pyrrolidin-2-one at 0 - 20℃; Product distribution / selectivity; |
Tri-n-octylamine
Diethyl tartrate
lansoprazole sulfide
lansoprasole
Conditions | Yield |
---|---|
With isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene | 0.63 g (29%) |
2,2,2-trifluoroethanol
lansoprasole
Conditions | Yield |
---|---|
Stage #1: 2,2,2-trifluoroethanol With potassium tert-butylate In N,N-dimethyl-formamide at 25 - 30℃; Stage #2: (R)-2-(4-methanesulfonyl-3-methyl-pyridin-2-ylmethanesulfinyl)-1H-benzimidazole In N,N-dimethyl-formamide at 25 - 30℃; for 24h; Stage #3: With acetic acid In water; N,N-dimethyl-formamide at 0 - 10℃; pH=7.0 - 7.5; |
lansoprasole
Conditions | Yield |
---|---|
Stage #1: C26H28F3N3O5S2 With sodium hydroxide In methanol; water at 30℃; for 0.916667h; Stage #2: With acetic acid pH=7; |
lansoprasole
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethyl acetate at 5 - 10℃; for 0.5h; |
lansoprasole
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethyl acetate at 5 - 10℃; for 0.5h; |
2-(chloromethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine
Benzimidazol-2-thiol
lansoprasole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water / Flow reactor 2: sodium hypochlorite; sodium hydroxide / water; acetonitrile / Flow reactor; Large scale View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide / 1,2-dimethoxyethane / 8 h / 50 °C 2: 3-chloro-benzenecarboperoxoic acid / chloroform / 0 °C View Scheme |
2-[p-(chlorosulfonyl)phenoxy]acetamide
lansoprasole
2-(4-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenoxy)acetamide
Conditions | Yield |
---|---|
Inert atmosphere; Basic conditions; | 96% |
With triethylamine In dichloromethane |
choline chloride
lansoprasole
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 20℃; for 24h; | 94% |
(4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester
lansoprasole
Conditions | Yield |
---|---|
With sodium hydride; sodium hydrogencarbonate In dichloromethane at 20℃; | 94% |
Stage #1: lansoprasole With sodium hydride In dichloromethane at 20℃; Inert atmosphere; Stage #2: (4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester With sodium hydrogencarbonate In dichloromethane Inert atmosphere; | 94% |
6-[2-(4-chlorosulfonyl-phenoxy)-acetylamino]-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester
lansoprasole
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane at 20℃; for 2h; | 94% |
2-[p-(chlorosulfonyl)phenoxy]-N-(2-pyridyl)acetamide
lansoprasole
2-(4-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}-phenoxy)-N-(2-pyridyl)acetamide
Conditions | Yield |
---|---|
Inert atmosphere; Basic conditions; | 94% |
With triethylamine In dichloromethane |
2-(4-chlorosulfonylphenoxy)butyric acid 2-(toluene-4-sulfonyl)ethyl ester
lansoprasole
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane at 20℃; for 2h; | 93% |
Stage #1: lansoprasole With sodium hydride In dichloromethane at 20℃; Inert atmosphere; Stage #2: 2-(4-chlorosulfonylphenoxy)butyric acid 2-(toluene-4-sulfonyl)ethyl ester In dichloromethane at 20℃; Inert atmosphere; | 93% |
lansoprasole
uracil
Conditions | Yield |
---|---|
In ethanol; water at 80℃; | 93% |
(R)-1,1'-Bi-2-naphthol
lansoprasole
Conditions | Yield |
---|---|
In dichloromethane at 20 - 40℃; Resolution of racemate; | 92.55% |
In dichloromethane at 20 - 40℃; | 92.55% |
In dichloromethane at 20 - 40℃; | 92.55% |
Conditions | Yield |
---|---|
In ethanol; water Reflux; | 89% |
3-chlorosulfonylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester
lansoprasole
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 87% |
[2-(morpholin-4-yl)ethoxy]benzene-4-sulfonyl chloride
lansoprasole
1-[{2-(morpholin-4-yl)ethoxy}phenyl-4-sulfonyl]-2-[(3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl)methylsulfinyl]-1H-benzimidazole
Conditions | Yield |
---|---|
Inert atmosphere; Basic conditions; | 82% |
With sodium hydrogencarbonate; triethylamine; sodium chloride In dichloromethane |
3-chlorosulfonylbenzoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester
lansoprasole
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane at 20℃; for 2h; | 80% |
Stage #1: lansoprasole With sodium hydride In dichloromethane at 20℃; Inert atmosphere; Stage #2: 3-chlorosulfonylbenzoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester In dichloromethane at 20℃; for 2h; Inert atmosphere; | 80% |
4-(4-chlorosulfonyl-3-isopropylphenoxyactamido)butyric acid 2-(3-nitrobenzenesulfonyl)ethyl ester
lansoprasole
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane at 20℃; for 2h; | 80% |
lansoprasole
1-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole
Conditions | Yield |
---|---|
With sodium hydroxide In water Heating; | 80% |
The Lansoprazole with CAS registry number of 103577-45-3 is also known as 1H-Benzimidazole, 2-(((3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl)methyl)sulfinyl)-. The IUPAC name is 2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-1H-benzimidazole. It belongs to product categories of Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds; Ion Pump Inhibitors; Monovalent Ion Channels; Voltage-gated Ion Channels; ATPase; Pharmaceutical Intermediates. In addition, the formula is C16H14F3N3O2S and the molecular weight is 369.36. This chemical is a white crystalline powder and should be sealed in cool place without light. What's more, it can be used for the treatment of duodenal ulcer embolism and it is a proton-pump inhibitor (PPI) which prevents the stomach from producing gastric acid.
Physical properties about Lansoprazole are: (1)ACD/LogP: 2.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.75; (4)ACD/LogD (pH 7.4): 2.76; (5)ACD/BCF (pH 5.5): 72.3; (6)ACD/BCF (pH 7.4): 72.89; (7)ACD/KOC (pH 5.5): 740.79; (8)ACD/KOC (pH 7.4): 746.86; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.635; (13)Molar Refractivity: 88.03 cm3; (14)Molar Volume: 245.8 cm3; (15)Surface Tension: 68.9 dyne/cm; (16)Density: 1.5 g/cm3; (17)Flash Point: 289.9 °C; (18)Enthalpy of Vaporization: 83.72 kJ/mol; (19)Boiling Point: 555.8 °C at 760 mmHg; (20)Vapour Pressure: 2.16E-12 mmHg at 25 °C.
Preparation of Lansoprazole: it is prepared by reaction of 2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethylsulfanyl]-1H-benzoimidazole. The reaction needs reagent m-chloroperbenzoic acid and solvent CHCl3 with other condition of ice-cooling. The yield is about 45%.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCC(F)(F)F
2. InChI: InChI=1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,
18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)
3. InChIKey: MJIHNNLFOKEZEW-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD | oral | > 2gm/kg (2000mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 387, 1993. | |
mouse | LD50 | intraperitoneal | > 5gm/kg (5000mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: MUSCLE WEAKNESS KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl, |
mouse | LD50 | oral | > 5gm/kg (5000mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl, |
mouse | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl, | |
mouse | LDLo | intravenous | 75mg/kg (75mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 24, Pg. 905, 1996. |
rat | LD50 | intraperitoneal | 5gm/kg (5000mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl, |
rat | LD50 | oral | > 5gm/kg (5000mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl, | |
rat | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl, | |
rat | LDLo | intravenous | 58mg/kg (58mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 24, Pg. 905, 1996. |
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